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WO2005097802A1 - Derives de quinoleine anneles comme pesticides - Google Patents

Derives de quinoleine anneles comme pesticides Download PDF

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Publication number
WO2005097802A1
WO2005097802A1 PCT/EP2005/003470 EP2005003470W WO2005097802A1 WO 2005097802 A1 WO2005097802 A1 WO 2005097802A1 EP 2005003470 W EP2005003470 W EP 2005003470W WO 2005097802 A1 WO2005097802 A1 WO 2005097802A1
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WIPO (PCT)
Prior art keywords
diyl
cyano
chlorine
hydroxy
fluorine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
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PCT/EP2005/003470
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German (de)
English (en)
Inventor
Robert Velten
Isabelle Adelt
Jutta BÖHMER
Jens Frackenpohl
Thomas Schenke
Peter Lösel
Olga Malsam
Christian Arnold
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Bayer CropScience AG
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Bayer CropScience AG
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Filing date
Publication date
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Priority to US11/547,529 priority Critical patent/US20080113994A1/en
Priority to JP2007506702A priority patent/JP2007532503A/ja
Priority to BRPI0509751-7A priority patent/BRPI0509751A/pt
Priority to EP05730943A priority patent/EP1735317A1/fr
Publication of WO2005097802A1 publication Critical patent/WO2005097802A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D497/04—Ortho-condensed systems

Definitions

  • the present application of an invention relates to new fused quinoline derivatives, the use of known and new fused quinoline derivatives as plant treatment agents, in particular for controlling animal pests, and plant treatment agents based on known and new fused quinoline derivatives.
  • Q 1 represents a single bond, O (oxygen), S (sulfur), NR 1 , CO, CS, CNR 1 or optionally substituted alkanediyl,
  • R 2 stands for H (hydrogen), hydroxy, amino, nitro, cyano, carboxy, carbamoyl, thioarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, dialkylaminocarbonyl or dialkylaminosulfonyl,
  • R 3 stands for H, hydroxy, amino, nitro, cyano, carboxy, carbamoyl, thioarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, dialkylaminocarbonyl or dialkylaminosulfonyl, or together with R 2 represents a benzo group or alkanediyl, oxaalkanediyl or dioxaalkanediyl,
  • R stands for H, hydroxy, amino, nitro, cyano, carboxy, carbamoyl, thioarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, dialkylaminocarbonyl or dialkylaminosulfonyl, or together with.
  • R 3 represents a benzo group or alkanediyl, oxaalkanediyl or dioxaalkanediyl,
  • R stands for H (hydrogen), hydroxy, amino, nitro, cyano, carboxy, carbamoyl, thioarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, dialkylaminocarbonyl or dialkylaminosulfonyl, or together with R 4 represents a benzo group or alkanediyl, oxaalkanediyl or dioxaalkanediyl,
  • R 6 represents H or optionally substituted alkyl
  • R 7 stands for H or for optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl and adducts or salts formed from the compounds of the formula (I) with acids or bases, have strong activity against animal pests.
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl can bond with heteroatoms, such as in alkoxy, also in conjunction • - to the extent possible in each case be branched or straight chain.
  • Optionally substituted radicals can be mono- or polysubstituted, whereby in the case of multiple substitution the substituents can be the same or different.
  • Halogen substituted residues such as e.g. Haloalkyl, can contain one or more halogen substituents. In the case of multiple substitution by halogen, these substituents can be the same or different.
  • Halogen stands for fluorine, chlorine, bromine or iodine, in particular for fluorine, chlorine or bromine.
  • Q 1 very particularly preferably represents a single bond, O (oxygen) or NR 1 or hydroxyl, fluorine, chlorine, methoxy or ethoxy. substituted methylene, ethane-l, l-diyl, ethane-l, 2-diyl (dimethylene), propane-l, l-diyl, propane-l, 2-diyl, 2-methyl-propane-l, 2-diyl or propane-2,2-diyl.
  • Q 2 very particularly preferably represents O (oxygen), S (sulfur), SO, S0 2 or hydroxyl, fluorine, chlorine, methoxy or ethoxy-substituted methylene, ethane-l, l-diyl, ethane-l, 2-diyl (Dimethylene), propane-l, l-diyl, propane-l, 2-diyl, 2-methyl-propane-l, 2-diyl or propane-2,2-diyl, but in each individual case Q 1 and Q 2 are different, unless they stand for A.
  • R 1 preferably represents H (hydrogen), hydroxyl, in each case optionally by hydroxy, cyano, halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C ⁇ -C -Alkylamino or di- (-C-C 4 alkyl) -amino substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having up to 6 carbon atoms in the alkyl groups, each optionally substituted by cyano or halogen Alkenyl, alkenyloxy, alkynyl or alkynyloxy each having up to 6 carbon atoms, in each case cycloalkyl, cycloalkylcarbonyl
  • heterocyclyl group being saturated or unsaturated, monocyclic or bicyclic and each containing up to 10 carbon atoms, 1 to 4 N atoms and / or an O atom and / or an S atom.
  • H hydrogen
  • hydroxy in each case optionally by
  • Pentinyl, propynyloxy, butynyloxy or pentynyloxy in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl-cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, Cyclopropyloxy, cyclobutyloxy, cyclopentyloxy or cyclohexyloxy, each optionally by nitro, hydroxyl, amino, cyano, carbamoyl,
  • Thiocarbamoyl fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, Chloroethyl, dichloroethyl, trichloroethyl, chlorofluoroethyl, chlorodifluoroethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, di-fluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, Dichlor
  • H hydrogen
  • hydroxy in each case methyl, ethyl, n- or i-propyl, acetyl, propionyl
  • n optionally substituted by hydroxy, cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy - or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, each optionally by Fluorine, chlorine or bromine-substituted propenyl, butenyl, propenyloxy, butenyloxy, propynyloxy, propyn
  • R 2 preferably represents H (hydrogen), hydroxy, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or each optionally by hydroxy, cyano, halogen, C 1 -C 4 alkoxy, C 1 -C 4 alkylamino or di- (C 1 -C 4 -alkyl) -amino substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, dialkylaminocarbonyl or dialkylaminosulfonyl each having up to 6 carbon atoms in the alkyl groups.
  • R 2 particularly preferably represents H (hydrogen), hydroxyl, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or each optionally by hydroxyl, cyano, fluorine, chlorine, methoxy, ethoxy, n - or i-propoxy, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio
  • R 2 very particularly preferably represents H (hydrogen), hydroxyl, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or each optionally by hydroxyl, cyano, fluorine, chlorine, methoxy, ethoxy, n - or i-propoxy, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, Methylamino, ethylamino,
  • R 3 preferably represents H (hydrogen), hydroxy, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or each optionally by hydroxy, cyano, halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylamino or Di- (C 1 -C 4 -alkyl) -amino substituted substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, dialkylaminocarbonyl or dialkylaminosulfonyl each having up to 6 carbon atoms in the alkyl groups, or together with R 2 for a benzo Grouping or alkanediyl, oxaalkanediyl or dioxaalkanediyl, each with up to 4 carbon atoms.
  • R 3 ' particularly preferably represents H (hydrogen), hydroxy, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or in each case optionally by hydroxy, cyano, fluorine, chlorine, methoxy, ethoxy, n - or i-propoxy, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n - or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-buty
  • R 3 very particularly preferably represents H (hydrogen), hydroxyl, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or each optionally by hydroxyl, cyano, fluorine, chlorine, methoxy, ethoxy, n - or i-propoxy, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethyl-thio, n - or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamin
  • R 4 preferably represents H (hydrogen), hydroxy, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for each optionally by hydroxy, cyano, halogen, C 1 -C 4 -alkoxy, C 1 -C 4 alkylamino or di- (-C 4 -alkyl) -amino substituted substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, dialkylaminocarbonyl or dialkylaminosulfonyl each having up to 6 carbon atoms in the alkyl groups, or • together with R 3 for one Benzo grouping or alkanediyl, oxaalkanediyl or dioxaalkanediyl, each with up to 4 carbon atoms.
  • R 4 particularly preferably represents H (hydrogen), hydroxyl, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or each optionally by hydroxyl, cyano, fluorine, chlorine, methoxy, ethoxy, n - or i-propoxy, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio
  • R 4 very particularly preferably represents H (hydrogen), hydroxyl, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or each optionally by hydroxyl, cyano, fluorine, chlorine, methoxy, ethoxy, n - or i-propoxy, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino,
  • R 5 preferably represents H (hydrogen), hydroxy, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or each optionally by hydroxy, cyano, halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylamino or Di- (-C 4 -alkyl) -amino substituted substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, dialkylaminocarbonyl or dialkylaminosulfonyl each having up to 6 carbon atoms in the alkyl groups, or together with R 4 for a benzo Grouping or alkanediyl, oxaalkanediyl or dioxaalkanediyl, each with up to 4 carbon atoms
  • R 5 particularly preferably represents H (hydrogen), hydroxyl, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or each optionally by hydroxyl, cyano, fluorine, chlorine, methoxy, ethoxy, n - or i-propoxy, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio
  • R 5 very particularly preferably represents H (hydrogen), hydroxyl, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or each optionally by hydroxyl, cyano, fluorine, chlorine, methoxy, ethoxy, n - or i-propoxy, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino,
  • R> 6 particularly preferably represents H (hydrogen) or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by hydroxyl, cyano or halogen.
  • R. very particularly preferably represents H (hydrogen) or methyl, ethyl, n- or i-propyl which is optionally substituted by hydroxy, cyano, fluorine or chlorine.
  • R 7 is preferably H (hydrogen), optionally substituted by hydroxy, cyano, halogen, C r C 4 -alkoxy, C 4 alkylthio, C 1 -C 4 alkylsulfinyl, Ci-C 4 alkylsulfonyl, CC 4 - Alkylamino or di- (-CC 4 -alkyl) -amino substituted alkyl having up to 6 carbon atoms, each optionally substituted by cyano, halogen or CC 4 alkyl substituted cycloalkyl or cycloalkylalkyl each having up to 6 carbon atoms in the cycloalkyl group and optionally up to 4 carbon atoms in the alkyl part, in each case optionally substituted by nitro, hydroxy, amino, cyano, carbamoyl, thiocarbamoyl, Phe ⁇ yl, phenoxy, benzyloxy, halogen, CC 6 - alkyl
  • heterocyclyl group being saturated or unsaturated, monocyclic or bicyclic is and each contains up to 10 carbon atoms, 1 to 4 N atoms and / or an O atom and / or an S atom.
  • R 7 particularly preferably represents H (hydrogen), in each case optionally through hydroxy, cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfmyl, ethylsulfinyl, Methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino substituted ized methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by cyano, fluorine, chlorine or methyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cycl
  • R 7 very particularly preferably represents H (hydrogen), in each case optionally methyl, ethyl, substituted by hydroxy, cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy . n- or i-propyl, in each case optionally substituted by fluorine, chlorine or methyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopenthenethyl or cyclohexylmethyl, each optionally ' by nitro, hydroxyl, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluoro
  • a very particularly preferred group are those compounds of the formula (I) in which the bond shown in broken lines is a double bond and A, Q 1 , Q 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given below:
  • A stands for methylene, ethane-1, l-diyl, ethane-1, 2-diyl (dimethylene), propane-1, l-diyl, propane-1, 2-diyl or 2-methyl-propane-1, 2 diyl.
  • Q 1 here stands for a single bond, for methylene, ethane-l, l-diyl, ethane-l, 2-diyl (dimethyl), propane-l, l-diyl, propane-l, 2-diyl or 2- Methyl-propane-l, 2-diyl, or for O (oxygen) or NR 1 , where R 1 is hydrogen, methyl, ethyl, n- or i-propyl, or phenyl.
  • Q 2 here stands for methylene, for O (oxygen), S (sulfur), SO, S0 2 or CO, but in each individual case Q 1 and Q 2 are different insofar as they do not stand for methylene,
  • R 1 here stands for H (hydrogen), in each case optionally substituted by hydroxy, cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, in each case optionally propylene, butenyl, propynyl or butynyl substituted by fluorine, chlorine or bromine, in each case optionally substituted by fluor
  • R 2 here stands for H (hydrogen), hydroxyl, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally with hydroxyl, cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-Propoxy, dimethylamino or diethylamino substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, dimethylamino , Dimethylaminocarbonyl or dimethylaminosulfonyl.
  • R 3 here stands for H (hydrogen), hydroxy, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by hydroxy, cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-Propoxy, dimethylamino or diethylamino substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl , Dimethylamino, Dimethylaminocarbonyl or Dimethylaminosulfonyl, or together with R 2 for a benzo grouping.
  • R 4 here stands for H (hydrogen), hydroxy, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally with hydroxy, cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-Propoxy, dimethylamino or diethylamino substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, dimethylamino , Dimethylaminocarbonyl or Dimethylaminosulfonyl, or together with R 3 for a benzo group or methylenedioxy.
  • R 5 here stands for H (hydrogen), hydroxy, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally with hydroxy, cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-Propoxy, dimethylamino or diethylamino substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, dimethylamino , Dimethylaminocarbonyl or Dimethylaminosulfonyl, or together with R 4 for a benzo grouping.
  • R 6 here stands for H (hydrogen) or for methyl, ethyl, n- or i-propyl which is optionally substituted by hydroxy, cyano, fluorine or chlorine.
  • R 7 here stands for H (hydrogen), in each case optionally substituted by hydroxy, cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy methyl, ethyl, n- or i-propyl, in each case optionally by fluorine, chlorine or Methyl-substituted cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally by nitro, hydroxy, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl , Chlorodifluoromethyl, fluoro
  • Another very particularly preferred group of the compounds are those compounds of the formula (I) in which
  • R and R4 together represent O-CH2-O, R 5 for H and R 6 for H.
  • Another very particularly preferred group of the compounds are those compounds of the formula (I) in which
  • Another very particularly preferred group of the compounds are those compounds of the formula (I) in which the
  • Dashed line in formula (I) represents a double bond.
  • Another very particularly preferred group of the compounds are those compounds of the formula (I) in which
  • R ' is substituted phenyl.
  • Examples of the compounds of the formula (I) to be used according to the invention are listed in Table 1 below.
  • the specified physical data are LC-MS measurements: m / z (%) / R t .
  • the measurements were carried out on an Agilent LC / MSD, consisting of an Agilent HPLC 1100 system with vacuum degasser, binary pump, column oven and diode array detector (DAD) and LC-MSD detector with ESI ion source.
  • Analytical column Dimension: 70 x 3.1 mm, column material: Kromasil C18, grain size: 3.5 ⁇ m.
  • Solvent A 0.1% formic acid in water;
  • Solvent B acetonitrile.
  • Gradient Starting conditions: 90% A / 10% B; the acetonitrile fraction (B) is increased from 10% / min to 5% A / 95% B; then another 5 min at 5% A / 95% B.
  • the fused quinoline derivatives of the formula (I) are suitable for the protection of plants and with good plant tolerance, favorable warm-blooded toxicity and good environmental compatibility Plant organs, to increase crop yields, improve the quality of the crop and to combat animal pests, in particular insects, arachnids and nematodes, in agriculture, in forests, in gardens and leisure facilities, in the protection of stocks and materials and in the hygiene sector occurrence. They can preferably be used as plant protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Thysanura e.g. Lepisma saccharina.
  • Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
  • Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.
  • Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chryso ⁇ hoea, Lymantria spp., Bucculatrix thurberiisisppiasppia, Phyllella.
  • Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chryso ⁇ hoea, Lymantria spp., Bucculatrix thurberiisisppiaspp
  • Otiorrhynchus sulcatus Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Giptusibbium psol. Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Scorpio maurus Latrodectus mactans, Acarus siro, Argas spp., Omithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyal ., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp ..
  • Plant parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaph.
  • the compounds of the formula (I) according to the invention are particularly notable for strong action against beetles and larvae thereof (for example Phaedon cochleariae), butterflies and larvae or caterpillars thereof (for example Heliothis virescens, Plutella xylostella, Spodoptera exigua, Spodoptera frugiperda), spider mites (for example Tetranychus urticae), and nematodes (e.g. Meloidogyne incognita).
  • beetles and larvae thereof for example Phaedon cochleariae
  • butterflies and larvae or caterpillars thereof for example Heliothis virescens, Plutella xylostella, Spodoptera exigua, Spodoptera frugiperda
  • spider mites for example Tetranychus urticae
  • nematodes e.g. Meloidogyne incognita
  • the compounds according to the invention can also be used in certain concentrations or application rates as herbicides or as safeners therefor, as microbicides, for example as fungicides, antifungal agents or bactericides. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoot, leaf, flower and root, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, habitat or location according to the customary treatment methods, for example by immersion, spraying, vaporization, atomizing, scattering, spreading, injecting and in the case of propagation material, in particular seeds. continue by wrapping one or more layers.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide and water.
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide and water.
  • Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, ma ⁇ nor, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifying and / or foaming agents are possible: e.g.
  • non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as dispersing agents are possible: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and
  • Lecithins and synthetic phospholipids can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, Fe ⁇ ocyanblau and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations in general contain between 0.1 and 95 wt .-% • active compound, preferably between 0.5 and 90%.
  • the active substance according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active substances, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • Hisecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
  • Ampropylfos Ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin;
  • bilanafos , binapacryl; biphenyl; bitertanol; Blasticidin-S; bromuconazole; Bupirimate;
  • Buthiobate butylamine; Calcium polysulfide; capsimycin; captafol; captan; carbendazim; carboxin; carpropamid; carvones; chinomethionat; Chlobenthiazone; Chlorfenazole; chloroneb;
  • chlorothalonil chlozolinate; Clozylacon; cyazofamid; cyflufenamid; cymoxanil; Cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen;
  • dimethomorph dimoxystrobin; diniconazole; Diniconazole-M; dinocap; diphenylamines; Dipyrithione; Ditalimfos; dithianon; dodine; Drazoxolon; edifenphos; epoxiconazole;
  • Fenbuconazole fenfuram; fenhexamid; Fenitropan; fenoxanil; fenpiclonil; fenpropidin;
  • fenpropimorph ferbam; fluazinam; Flubenzimine; fludioxonil; flumetover; flumorph;
  • fluoromides fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil; flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; Furcarbanil;
  • Imibenconazole Iminoctadine triacetate; Iminoctadine tris (albesilate); iodocarb; ipconazole;
  • iprobenfos iprodione; iprovalicarb; Irumamycin; isoprothiolane; Isovaledione; kasugamycin; Kresoxim-methyl; mancozeb; maneb; Meferimzone; mepanipyrim; mepronil; metalaxyl;
  • Metalaxyl-M metconazole; methasulfocarb; Methfuroxam; metiram; metominostrobin;
  • phosdiphen phthalides; picoxystrobin; piperalin; Polyoxins; Polyoxorim; Probenazole; prochloraz;
  • procymidone propamocarb; Propanosine-sodium; propiconazole; propineb; proquinazid;
  • prothioconazole pyraclostrobin; Pyrazohos; pyrifenox; pyrimethanil; pyroquilon; Pyroxyfur;
  • trifloxystrobin triflumizole; triforine; triticonazole; Uniconazole; Validamycin A; vinclozolin;
  • copper salts and preparations such as Bordeaux mixture; Copper hydroxide; Copper naphthenate; Copper oxychloride; Copper sulfate; Cufraneb; Cuprous oxide; mancopper; Oxine-copper.
  • DDT Deltamethrin, Demeton-S-methyl, Demeton-S-methylsulphone, Diafenthiuron, Dialifos, Diazinone, Dichlofenthion, Dichlorvos, Dicofol, Dicrotophos, Dicyclanil, Diflubenzuron, Dime- fluthrin, Dimetho Dinot, Dinobutonate, Dinobutonate, Dimobutinate, Dinobutinate, Dimobutinate, Dimobutinate Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn, DOWCO-439,
  • Gamma-cyhalothrin gamma-HCH, gossyplure, grandlure, granulovirus
  • Halofenozide HCH, HCN-801, Heptenophos, Hexaflumuron, Hexythiazox, Hydra-methylnone, Hydroprene, IKA-2002, Imidacloprid, Imiprothrin, Indoxacarb, Iodofenphos, Iprobefos, Isazofos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin,
  • Mecarbam Malathion, Mecarbam, Mesulfenfos, Metaldehyde, Metam-sodium, Methacrifos,. Methamidophos, metharhilic anisopliae, metharhitic flavoviride, methidathione, methiocarb, methomyl, methoprene, methoxychlor, methoxyfenozide, metofluthrin, metolcarb, metoxadiazone, mevinophos, milbemectin, milbemycin, MKI-245, MON-Rotophosos, MT-monocinophinos, MT-45700
  • NC-104 NC-170, NC-184, NC-194, NC-196, Niclosamide, Nicotine, Nitenpyram, Nithiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768, Novaluron, Noviflumuron,
  • Paecilomyces fumosoroseus Parathion-methyl, Parathion (-ethyl), Permethrin (eis, trans-), Petroleum, PH-6045, Phenothrin (IR-trans isomer), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Piperonyl butoxide, Pirimicarb, Pirimiphos-methyl, Pirimiphos-ethyl, Potassium oleate, Prallethrin, Profenofos, Profluthrin, Promecarb, Propaphos, Propargite, Propetamphos, Propoxur, Prothiofos, Prothoate, Protrifenbute, Pyymmetclhrin, Pyrometrozhrin, Pyrometrozhrin Pyridaben, pyridalyl, pyridaphenthion, pyridathione, pyr
  • the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms prepared from these formulation formulations in a mixture with synergists.
  • Synergists are compounds by which the action of the active ingredients is increased without the added synergist itself having to be active.
  • the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in mixtures with inhibitors which reduce degradation of the active compound after use in the environment of the plant, on the surface of parts of plants or in plant tissues ,
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application form.
  • the active compound When used against hygiene pests and pests of stored products, the active compound is distinguished by an outstanding residual action on wood and clay and by a good stability to alkali on limed substrates.
  • plants and their parts can be treated.
  • plant species and plant cultivars and their parts occurring wildly or obtained by conventional biological breeding methods, such as crossing or protoplast fusion are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetic modified organisms) and their parts are treated.
  • the term "parts" or "parts of plants" or “plant parts” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with new properties (“traits”) which have been grown both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and / or widening the spectrum of action and / or an increase in the action of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvest products, higher shelf life and / or workability of the harvest products possible, which go beyond the expected effects.
  • the preferred transgenic plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher crop yields, higher quality and / or higher yields. nutritional value of the crop products, higher shelf life and / or workability of the crop products. Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients.
  • transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes , Cotton, tobacco and rapeseed are highlighted.
  • the traits are particularly emphasized as the plants' increased defense against insects, arachnids, nematodes and snails due to the toxins produced in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (e.g.
  • Bt plants by the genes Cry ⁇ A (a) , Cry ⁇ A (b), Cry ⁇ A (c), CryllA, CrylUA, CryHIB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”.
  • the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • the properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene).
  • the genes conferring the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • Examples of "Bt plants” are maize varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready® (tolerance to glyphosates, e.g. maize, cotton, soybeans), Liberty Link® (tolerance to phosphinotricin, e.g. rapeseed), IMI® ( Tolerance to imidazolinones) and STS® (tolerance to sulfonylureas such as maize).
  • the herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (eg maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • the plants listed can be treated according to the invention in a particularly advantageous manner with the compounds of the general formula I or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the active compounds according to the invention act not only against pests from plants, hygiene and stored products, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas.
  • animal parasites ectoparasites
  • tick ticks leather ticks
  • mites running mites
  • flies stinging and licking
  • parasitic fly larvae lice, hair lice, Featherlings and fleas.
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..
  • Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota ., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Glossina spp., Calliphora spp., Glossina spp.,
  • Siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..
  • Actinedida Prostigmata
  • Acaridida Acaridida
  • Acarapis spp. Cheyletiella spp., Omithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp.
  • Tyrophagus spp. Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
  • the active compounds of the formula (I) according to the invention are also suitable for combating arthropods which are used in agricultural animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice.
  • arthropods By combating these arthropods, deaths and reduced performance (in the case of meat, milk, wool, skins, eggs, honey, etc.) are to be reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry.
  • the active compounds according to the invention are used in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing , the powder and with the help of active substance-containing shaped bodies, such as collars, ear tags, tail tags, limb straps, holsters, marking devices, etc.
  • enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories
  • parenteral administration for example by Injections (intr
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or use it as a chemical bath.
  • formulations for example powders, emulsions, flowable agents
  • insects may be mentioned by way of example and preferably, but without limitation:
  • Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;
  • Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;
  • Bristle tails such as Lepisze saccharina.
  • non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, wood processing products and paints.
  • the material to be protected from insect infestation is very particularly preferably wood and wood processing products.
  • Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing it are to be understood as examples:
  • the active compounds can be used as such, in the form of concentrate formulations or generally customary formulations, such as powders, granules, solutions, suspensions, emulsions or pastes.
  • the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments and further processing aids.
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active ingredient according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
  • the amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimum amount of use can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.
  • the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
  • Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, turpentine oil and Like. Used.
  • liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C. and / or locker oil and / or monochloronaphthalene, preferably ⁇ -monochlomaphthalene, are used.
  • organic non-volatile oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
  • part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced.
  • hydroxyl and / or ester and / or Aliphatic organic chemical solvents containing ether groups such as, for example, glycol ethers, esters or the like, are used.
  • organic-chemical binders Acrylate resin, a vinyl resin, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin used.
  • a vinyl resin e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin used.
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
  • Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
  • binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, higher glycerol glycol or glycerol ether and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
  • phosphoric acid esters such as tributyl phosphate
  • adipic acid esters such as di- (2-ethylhexyl) adipate
  • stearates such as butyl stearate or amyl
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Water is also particularly suitable as a solvent or diluent, optionally in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved by industrial impregnation processes, e.g. vacuum, double vacuum or pressure processes.
  • the ready-to-use compositions may optionally contain further insecticides and, if appropriate, one or more fungicides.
  • insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional mixing partners.
  • the compounds mentioned in this document are an integral part of the present application.
  • Insecticides such as Chlo ⁇ yriphos, Phoxim, Silafluofm, Alphamethrin, Cyfluthrin, Cypermethrin, Delta ethrin, Permethrin, Imidacloprid, NI-25, Flufenoxuron, Hexaflumuron, Transfluthrin, Thiaclopideon, Triflumididine, Trifloxidone, Trifloxidone, Trifloxidine, Trifloxidone, Trifloxidone, Trifloxidone, Trifloxidone, Trifloxidone, Trifloxidone, Trifloxidone, Trifloxidone, Trifluoride
  • fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluoride, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5 -N-octylisothiazolin-3-one.
  • the compounds according to the invention can be used to protect objects, in particular hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water.
  • Ledamo ⁇ ha barnacles
  • Balanomo ⁇ ha barnacles
  • Baianus or Pollicipes species increases the frictional resistance of Ships and subsequently leads to a significant increase in operating costs due to increased energy consumption and, moreover, frequent dry dock stays.
  • the compounds according to the invention alone or in combination with other active ingredients, have an outstanding antifouling effect.
  • heavy metals such as, for example, in bis (trialkyltin) sulfides, tri-M-butyltin laurate, tri-ra-butyltin chloride, copper (I) oxide, triethyltin chloride, Tri-R-butyl (2-phenyl-4-chl ⁇ henoxy) tin, tributyltin oxide ,.
  • the ready-to-use antifouling paints may also contain other active ingredients, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
  • Suitable combination partners for the antifouling agents according to the invention are preferably:
  • Algicides such as 2-tert-butylamino-4-cyclopropylamino-6-methylthio-l, 3,5-triazine, dichlorophene, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;
  • Fungicides such as benzo [ ⁇ ] thiophenecarboxylic acid cyclohexylamide-S, S-dioxide, dichlofluanid, fluorofolpet, 3-iodo-2-propynylbutylcarbamate, tolylfluanid and azoles such as azaconazole, cyproconazole, epoxyconazole, hexaconazole, metazazole, metconazole;
  • Molluscicides such as fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb and trimethacarb, Fe-chelates,
  • antifouling agents such as 4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulfone, 2- (N, N-dimethylthiocarbamoylthio) -5-nitrothiazyl, potassium, copper,
  • the antifouling agents used contain the active compound according to the invention of the compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular of 0.01 to 20% by weight.
  • the antifouling agents according to the invention furthermore contain the usual constituents as described, for example, in Uhgerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.
  • antifouling paints contain in particular binders.
  • Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, in particular in an aqueous system, vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / - styrene / acrylonitrile rubbers, drying agents Oils such as linseed oil, resin esters or modified hard resins in combination with tar or bitumen, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
  • Paints may also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in seawater. Paints may also contain materials, such as rosin, to enable controlled release of the active ingredients.
  • the paints may also contain plasticizers, theological properties modifiers and other conventional ingredients.
  • the compounds according to the invention or the abovementioned mixtures can also be incorporated into self-polishing antifouling systems.
  • the active ingredients are also suitable for controlling animal pests, in particular insects, arachnids and mites, which live in closed spaces such as apartments, factory halls, offices, vehicle cabins, etc. occurrence. To combat these pests, they can be used alone or in combination with other active ingredients and auxiliaries in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
  • Sco ⁇ ionidea e.g. Buthus occitanus.
  • Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Omithodorus moubat, RJfiipicephalus sanguineus, Trombicula alfreddugesi, ⁇ eutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides for
  • Diplopoda e.g. Blaniulus guttulatus, Polydesmus spp.
  • Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia inte ⁇ unctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • Ctenocephalides canis Ctenocephalides felis, Pulex i ⁇ itans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera for example Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramoriu caespitum.
  • anoplura for example Pediculus humanus capitis, Pediculus humanus co ⁇ oris, Phthirus pubis.
  • Example 1 The compound listed as Example 1 in Table 1 (above) can be prepared, for example, as follows:
  • Example 107 The compound listed in Table 1 (above) as Example 107 can be produced, for example, as follows:
  • Example 8 in Table 1 can be prepared, for example, as follows:
  • Example 32 the compound listed in Table 1 (above) as Example 32 can be made as follows:
  • Example 25 in Table 1 can be prepared, for example, as follows:
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Chinese cabbage leaf slices (Brassica pekinensis) are sprayed with an active ingredient preparation of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
  • the effect is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • Example B Spodoptera frugiperda test (spray treatment)
  • Solvent 78 parts by weight of acetone; 1.5 parts by weight of dimethylformamide
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Corn leaf disks (Zea mays) are sprayed with an active ingredient preparation of the desired concentration and, after drying, are infested with larvae of the army worm (Spodoptera frugiperda). After the desired time, the effect is determined in%. 100% means that all larvae have been killed; 0% means that no larvae have been killed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and, after drying, are populated with larvae of the cockroach (Plutella xylostella).
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no larvae have been killed.
  • Example D Heliothis virescens egg test (spray treatment)
  • Solvent 78 parts by weight of acetone; 1.5 parts by weight of dimethylformamide
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Soybean leaves (Glycine max) are sprayed with an active ingredient preparation of the desired concentration and, after drying, are populated with eggs from the cotton capsule worm (Heliotis virescens).
  • the effect is determined in%. 100% means that no larvae have hatched; 0% means that the hatching of the larvae corresponds to that in the untreated control.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and, after drying, are infested with larvae of the army worm (Spodoptera exigua). After the desired time, the kill is determined in%. 100% means that all larvae have been killed; 0% means that no larvae have been killed.
  • Example F Tetranychus test (OP resistant / spray treatment)
  • Solvent 78 parts by weight of acetone; 1.5 parts by weight of dimethylformamide
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Bean leaf slices Phaseolus vulgaris
  • Triticae Tricholine dexase
  • Bean leaf slices Phaseolus vulgaris
  • which are affected by all stages of the common spider mite Tetranychus urticae
  • an active ingredient preparation of the desired concentration is sprayed with an active ingredient preparation of the desired concentration.
  • the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
  • Example G Meloidogyne test (spray treatment)
  • active compound 1 part by weight of active compound is mixed with the one specified. Amount of solvent and dilute the concentrate with water to the desired concentration.
  • Vessels are filled with sand, active ingredient solution, Meloidogyne incognita egg larva suspension and lettuce seeds.
  • the lettuce seeds germinate and the plantlets develop.
  • the galls develop at the roots.
  • the nematicidal effect is determined in% using the formation of bile. 100% means that no galls were found; 0% means that the number of galls on the treated plants corresponds to that in the untreated control.
  • Example H Myzus test (spray treatment)
  • Solvent 78 parts by weight of acetone, 1.5 parts by weight of dimethylformamide emulsifier: 0.5 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Chinese cabbage leaf slices (Brassica pekinensis), which are affected by all stages of the green peach aphid (Myzus persicae), are sprayed with an active ingredient preparation of the desired concentration.
  • the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.

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  • Chemical & Material Sciences (AREA)
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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

La présente invention concerne l'utilisation de dérivés de quinoléine de formule (I), dans laquelle la liaison en pointillé désigne une liaison simple ou double et les substituants ont la signification indiquée dans la description, comme produits phytosanitaires, en particulier pour la lutte contre les parasites animaux. Cette invention concerne également des produits phytosanitaires à base de dérivés de quinoléine annelés nouveaux et connus ainsi que de nouveaux dérivés de quinoléine.
PCT/EP2005/003470 2004-04-08 2005-04-02 Derives de quinoleine anneles comme pesticides Ceased WO2005097802A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US11/547,529 US20080113994A1 (en) 2004-04-08 2005-04-02 Annelated Quinoline Derivatives As Pesticide
JP2007506702A JP2007532503A (ja) 2004-04-08 2005-04-02 殺虫剤としての有環キノリン誘導体
BRPI0509751-7A BRPI0509751A (pt) 2004-04-08 2005-04-02 derivados de quinolina anelados como pesticidas
EP05730943A EP1735317A1 (fr) 2004-04-08 2005-04-02 Derives de quinoleine anneles comme pesticides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004017435A DE102004017435A1 (de) 2004-04-08 2004-04-08 Annellierte Chinolinderivate
DE102004017435.0 2004-04-08

Publications (1)

Publication Number Publication Date
WO2005097802A1 true WO2005097802A1 (fr) 2005-10-20

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Country Status (8)

Country Link
US (1) US20080113994A1 (fr)
EP (1) EP1735317A1 (fr)
JP (1) JP2007532503A (fr)
KR (1) KR20070011448A (fr)
CN (1) CN1964977A (fr)
BR (1) BRPI0509751A (fr)
DE (1) DE102004017435A1 (fr)
WO (1) WO2005097802A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11098052B2 (en) * 2016-03-02 2021-08-24 Arizona Board Of Regents On Behalf Of Arizona State University 4-azapodophylotoxins compounds

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103261170B (zh) 2010-12-24 2016-08-24 住友化学株式会社 稠杂环化合物及其用于害虫防治的用途
JP6168055B2 (ja) * 2012-06-18 2017-07-26 住友化学株式会社 縮合複素環化合物
CN111039950B (zh) * 2019-12-04 2021-03-23 江西中医药大学 一种生物碱化合物及其制备方法和用途
CN113717184B (zh) * 2021-08-19 2023-04-11 云南省烟草农业科学研究院 雪茄烟中一种具有抗烟草花叶病毒活性的喹啉生物碱及其制备方法和应用
CN114989180B (zh) * 2022-05-26 2024-06-04 广东海洋大学 杨叶肖槿内生真菌来源的化合物及其制备方法与应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3282943A (en) * 1961-11-14 1966-11-01 Boehringer Sohn Ingelheim N-substitution products of polymethylene-tetrahydroquinolines
WO2003001968A2 (fr) * 2001-06-26 2003-01-09 Beth Israel Deaconess Medical Center Compositions et procedes prohibant l'activation plaquettaire et la thrombose
WO2003064385A2 (fr) * 2002-02-01 2003-08-07 Bayer Cropscience Ag Delta1-pyrrolines
WO2004000842A1 (fr) * 2002-06-19 2003-12-31 Janssen Pharmaceutica, N.V. Derives substitues de 2,4-dihydro-pyrrolo (3, 4-b) -quinolin-9-one utilises comme inhibiteurs de la phosphodiesterase

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3282943A (en) * 1961-11-14 1966-11-01 Boehringer Sohn Ingelheim N-substitution products of polymethylene-tetrahydroquinolines
WO2003001968A2 (fr) * 2001-06-26 2003-01-09 Beth Israel Deaconess Medical Center Compositions et procedes prohibant l'activation plaquettaire et la thrombose
WO2003064385A2 (fr) * 2002-02-01 2003-08-07 Bayer Cropscience Ag Delta1-pyrrolines
WO2004000842A1 (fr) * 2002-06-19 2003-12-31 Janssen Pharmaceutica, N.V. Derives substitues de 2,4-dihydro-pyrrolo (3, 4-b) -quinolin-9-one utilises comme inhibiteurs de la phosphodiesterase

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11098052B2 (en) * 2016-03-02 2021-08-24 Arizona Board Of Regents On Behalf Of Arizona State University 4-azapodophylotoxins compounds

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EP1735317A1 (fr) 2006-12-27
CN1964977A (zh) 2007-05-16
DE102004017435A1 (de) 2005-11-03
JP2007532503A (ja) 2007-11-15
US20080113994A1 (en) 2008-05-15
BRPI0509751A (pt) 2007-10-23
KR20070011448A (ko) 2007-01-24

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